It's probably very obvious by now, but there's something to be said about companies with the "SF Quirky" vibes:
- The OS Redesign
- "Sexy Legal Documents"
- Emails with "<relevant hedgehog meme goes here>" as the subject line
- Having a merch shop with action figures of your CEO
It works both ways. When you're looking for adoption and making very pro-user moves, I guess it can be a benefit. However, when you're now looking to grow revenue and making very anti-user moves, it's insult to injury.
I'm the last person to say that tech "shouldn't be fun" or something overly-broad like that, but if your messaging doesn't match the decisions of leadership, you're gonna have a bad time.